1-Chloroethyl chloroformate → HCID 89602350, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-benzyl-4-(thiophen-2-ylmethyl)-1,2,3,6-tetra hydropyridine (1) (3.3 g, 12.26 mmol) in dichloromethane (30 mL) was added 1-chloroethyl chloroformate (12.27 g, 85.87 mmol) at 0° C. and the reaction mixture was allowed to stir at 20-35° C. for 3 h. Then the reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was rotary evaporated to get residue; which was dissolved in methanol (20 mL) and heated at 70-80° C. for 1 h. The reaction mixture was rotary evaporated under vacuum to get residue which was triturated with diethyl ether to get the desired compound as a brown solid (2.5 g); 1H NMR (400 MHz, DMSO-d6) δ 9.04-8.92 (m, 2H), 7.38 (dd, J=1.5, 5.4 Hz, 1H), 6.97 (dd, J=3.4, 5.4 Hz, 1H), 6.90 (dd, J=1.0, 3.4 Hz, 1H), 5.54 (s, 1H), 3.56 (s, 2H), 3.54-3.52 (m, 2H), 3.14-3.11 (m, 2H), 2.24-2.16 (m, 2H).

Provenance & Evidence